Punishing Cassandra

“Welcome back, Master Beta”, Maria greeted me. “Your dinner is ready.”

This time the meal was more modest compared to last night or even this morning. Perhaps this was taking my fight tomorrow into consideration, or it is simply because the other girls have devoured most of it. Sanakia was the only one who had yet eaten.

“You really don't have to wait on me”, I said while sitting down.

“Nonsense, my lord! Waiting on you is an honor!”, Sanakia quickly stated.

“One you got all to yourself”, Beatrice sighed pleasantly as she gobbled up the last remaining slices of what used to be a large strawberry cake.

“Yer getting fat, if you keep eating like that, Rice.”

“I don’t need to hear that from Miss devours an entire ham!”

“I-I split that with Aiju!”

Maria smiled at me. “As it happens Master Beta...we also prepared a different sort of meal for you.”

...what?

Moving into the so called playroom, sure enough there she was. Cassandra, strapped above some sort of restraining device, that put her butt into perfect penetration position.

“Welcome back, daddy”, Cassandra greeted me, her voice dripping with sarcasm.

“Is this to your liking, Master Beta? We can do some adjustments if you wish. Perhaps you would like to make use of some of our prime dildos?”, she asked with a cheerful smile.

Once again I had no idea what to say. This was just intended to be a joke! Of course I plan to punish Cassandra at some point but...

“Daddy.” As if she could read my thoughts, Cassandra interrupted me. “Just get on with it. You choose me, so come on.”

This is ridiculous.

My mischievous maid bowed politely. “Do you wish for me to remain, Master Beta?”

The last thing I needed was someone watching over my shoulder while I...whatever the hell this will turn out so I send Maria away. And that was that. Just me and Cassandra's butt.

“Are you comfortable?”, I asked while putting a hand on her ass. I had to admit it felt nice. Firm and bouncy at the same time. No one could fault Cassandra for neglecting her training.

“I had worse”, came the quick reply. “Are you going to fuck me or not?”

I gave her butt a slap, just to see her reaction.

“Hm, need to do harder then that, Daddy.”

Ugh.

Sure I could spank her. Fuck her in the ass. Penetrate her with all kinds of toys.

But I don’t really want to.

It probably goes without saying but If I really wanted to punish Cassandra, I would have to go hard. My usual punishments wouldn’t even faze her.

Just as most of her body, her butt was full of healed scars. I absentmindedly traced some of them. It goes without saying that Cassandra had a rough life. It doesn’t excuse what she did but I could understand how she turned out like this.

“Let me guess. All torn up about my scars? You want to punish me but you just can’t help but feel bad about me, can’t you?”, Cassandra chuckled. “Your so fucking predictable, Daddy.”

I talked a big game earlier but at the end of the day, Cassandra hit the mark. I suck when it comes to stuff like this.

Ok.

Then let’s go in a direction she does not expect.

“Remember our fight in the second round?”

“What stupid question is that? Of course I remember!”

“I am curious about what happened to you in that black void. Mind telling me?”

“More bedtime stories? Come on. I’m not your mom, daddy.” But I could tell Cassandra was stiffening. This wasn't something she wanted to recall. “Can't you just fuck me in the ass instead? Just grab the largest dildo on the shelf and cram it up without lube.”

She wiggled her butt enticingly but that only confirmed to me that this was the proper way forward.

“No, but answer honestly, will retelling this be traumatic for you?”

“Fuck no”, Cassandra quickly spat back. “That shit with...Don was traumatic. This is just...”

“just?”

“...you know.”

No, I don’t know. Wait, was Cassandra actually embarrassed for once? I don’t think I saw her blush a single time, well I guess technically I don’t now either because of ass but still.

I had to chuckle and gave her butt another slap. “Looks like we found the perfect punishment for you after all. Speak. And don’t spare the details.”

…

..

.

Where the hell was I?

Everything was dark and it feels like I'm floating? As I was trying to get my bearings, a bright light temporarily blinded me. And sure enough, there was the fucking devil, sitting on a throne.

“Welcome, Cass! So nice to have you here!”

Oh fuck.

“Where the fuck am I?”, I growled.

The devil bitch grinned. “Why, my own dimension of course! But for abbreviations sake lets just call it void. Here’s the pitch: You are going to stay here until you are ready to accept my clients terms.”

“That's not going to happen”, I responded immediately. “Why don’t you save us the trouble and...”

The Devil snapped her finger and something gross started to wrap itself around my arms and legs. Tentacles?

“I'm Femto by the way.” The devil introduced herself as she slowly got up from the throne and pranced towards me, the light following her as if she was some fancy diva. “You're a dom?”

“The fuck are you on about?”

The bitch grinned. “Just asking.” She brushed her hand against my stomach. “Breaking dom's can be quite fun. Yes, yes, I know one shouldn't mix business and pleasure but come on! You got to live a little!”

She snapped her finger and another tentacle started to slowly rub itself against my cunt. The disgusting feeling made me wince. “So Cass, Question: Do you want me to break you?”

“Do your worst, girl.” I glared at her. “I already went through hell. There is nothing you can do to me that I haven’t experienced yet.”

“Edgy.”, the devil nodded towards the tentacle. “And I get it. Your a tough girl. You have quite the wealth of experience. Yeah, I can dig that.” She grinned again. “In that case, lets take our time, shall we? I happen to have a lot of that in inventory.”

And just like that the devil bitch and her light vanished, leaving me alone with her squirming tentacles.

Ok, Cass. Calm down. Analyze the situation.

This is edging. Fairly standard stuff.

The room or void I was in was completely dark. But that's also just **** 101. Sensory deprivation.

Tentacles restrained me on all my limbs. I have some wiggle room but that’s clearly intentional, trying to free myself will only make my predicament worse.

The problem was that I had no concept of time, no idea how long this will go on. I doubt I can just outrun the clock. This devil has a way to fuck with time.

All the while the pressure was constantly building. Fuck. “Oi, devil, lets make a deal!”

Nothing.

I had to grin. So, she doesn't even allow me to bargain, eh? I should have accepted that first offer to surrender. Now I'm getting punished for my insolence. “Fuck me.”

How the fuck did that little shit got a devil at his disposal? No sane person would make a deal just to win a fucking tournament fight. Was he just tricked into using a devil box? I had to laugh. This was just too funny! All this preparation, all this careful assessment of my enemies.

All down the drain.

Because my opponent is a stupid, fucking idiot.

I shuddered as the tentacle briefly increased its intensity. Yes, it's not always the same, it seems to align itself to my emotion and feelings. Of course, never enough to actually get me over the edge. A constant tease.

I can see how this could drive someone mad. But if I lose my mind, I won't be able to surrender. No, this can’t be what the devil was after. Confident in this, I held out. But even so, it took an eternity. Long enough for my bladder to relieve itself and long enough for me to doubt my own judgment.

What if she leaves me her for days? Months.

Years?

In complete darkness with only these tentacles as company?

...

“Yo, are we having fun?”

How much time has passed?

Regardless. There she was. The devil hovered over me with her usual grin. “Looks like little Cass had an accident or ten, naughty girl. You should have told me that you need to go potty.”

I remained silent. I wasn't a stranger to ****. Saying anything here might very well cause her to fuck off.

“Soooo”, the devil mused. “That's some nice, sexual frustration I'm sensing from you. You are pretty pent up right now, aren't you? Would widdle Cass like to cum?”

“What’s with the baby talk?”, I growled, so annoyed that I couldn’t help myself. “That’s your kink?”

“Oh, Cass!”, The devil laughed and patted me on the shoulder. “The real question is what isn’t my kink. “I asked you a question.”

“I’m horny as fuck”, I replied truthfully.

“Nah, not yet”, the devil decided. “You still have no idea what it means to be really ****.”

“I still like to cum”, I responded dryly.

The devil studied my face for an agonizing long time. Then she chuckled. “I like you, Cass. You have pizaz! I can respect that. I really do.”

Of course that didn’t mean that the bitch would let me cum.

“Tell you what. I'm feeling very nice today, so special offer: I give you another chance to surrender, way before I usually would. What do you say to that?”

“T-thank you. I would like that.”

“Now, Cass. I’m taking a big risk here. I usually don’t do this. It’s not good business you know?”, the devil gave me a thumbs up. “But I think we have a pretty good thing going on here. So, to heck with business 101 and all that! Now, when we get back out there I need you to surrender to my client without fuss, got it? Don’t try to get cute, don’t try to play hardball. Because If I regret that trust I now place in you, I make sure you will regret it way more then I do. So, for your own sake, don’t you mess with me.”

I nodded demurely. “Y-yes, you made your point, I will not betray your trust.” And just like that we where back in the arena. I squinted as the bright light blinded me.

“Now then, Cass. You know what you have to say”, the devil demanded.

I looked at the devil and smiled. “Go fuck yourself, you stupid piece of shit devil bitch.”

The devil bitch sighed. “Unbelievable. My apologies, Sir. The other party is very uncooperative. But, I get the deal closed. No worries.”

And just like that we where back in the void.

The hell bitch let out another long sigh. “Cass, Cass, Cass, I am so very disappointed in you. I thought we had an arrangement?”

I chuckled. “Yeah, go fuck yourself. For a devil you sure as hell are green. Still new on the job?”

The devil stared at me and for the first time I felt that her facade was cracking, if only a little bit. I made her angry, I knew it. “I WAS willing to let you off easy, but lets start the real ****, shall we?”

I mentally prepared myself for what's to come as the devil snapped her finger once more.